5-Oxazolidinecarboxylic acid, 4-(4-methoxyphenyl)-2-oxo-, (4R,5R)-

Base Information

• Chemical Name: 5-Oxazolidinecarboxylic acid, 4-(4-methoxyphenyl)-2-oxo-, (4R,5R)-
• CAS No.: 691410-75-0
• Molecular Formula: C₁₁H₁₁NO₅
• Molecular Weight: 237.212
• Mol file: 691410-75-0.mol

Synonyms:

Chemical Property of 5-Oxazolidinecarboxylic acid, 4-(4-methoxyphenyl)-2-oxo-, (4R,5R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-Oxazolidinecarboxylic acid, 4-(4-methoxyphenyl)-2-oxo-, (4R,5R)-

There total 16 articles about 5-Oxazolidinecarboxylic acid, 4-(4-methoxyphenyl)-2-oxo-, (4R,5R)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

tert-butyl (E)-3-(4-methoxyphenyl)prop-2-enoate (53484-52-9) → (4R,5R)-4-(4-methoxyphenyl)-1,3-oxazolidine-2-one-5-carboxylic acid (691410-75-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: tetrahydrofuran; hexane / 2 h / -78 °C

1.3: 79 percent / (+)-(camphorsulfonyl)oxaziridine / tetrahydrofuran; hexane / -78 - 20 °C

2.1: 96 percent / H₂ / Pearlman's catalyst / methanol / 24 h / 3800 Torr

3.1: 36 percent / DMAP / tetrahydrofuran / 24 h / 20 °C

4.1: TFA / CH₂Cl₂ / 1 h / 20 °C

With dmap; n-butyllithium; hydrogen; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane;

DOI:10.1039/b402437k

Reference yield:

tert-butyl (R,R,R)-2-hydroxy-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-(4'-methoxyphenyl)propanoate (714951-38-9) → (4R,5R)-4-(4-methoxyphenyl)-1,3-oxazolidine-2-one-5-carboxylic acid (691410-75-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / H₂ / Pearlman's catalyst / methanol / 24 h / 3800 Torr

2: 36 percent / DMAP / tetrahydrofuran / 24 h / 20 °C

3: TFA / CH₂Cl₂ / 1 h / 20 °C

With dmap; hydrogen; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1039/b402437k

Reference yield:

3-(4-methoxy-phenyl)acrylic acid methyl ester (3901-07-3) → (4R,5R)-4-(4-methoxyphenyl)-1,3-oxazolidine-2-one-5-carboxylic acid (691410-75-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 72 percent / (DHDQ)2PHAL; LiOH*H₂O / K₂[OsO₂(OH)4] / 2-methyl-propan-2-ol / 20 h / 4 °C

2: 70 percent / triethylamine / CH₂Cl₂ / 0 °C

3: 60 percent / DIPEA / CHCl₃ / 48 h / 60 °C

4: aq. HCL / 1.5 h / Heating

5: NaOH / H₂O / 0 °C

With hydrogenchloride; lithium hydroxide; sodium hydroxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; N-ethyl-N,N-diisopropylamine; K2; In dichloromethane; chloroform; water; tert-butyl alcohol; 1: Sharpless asymmetric aminohydroxylation;

DOI:10.1016/j.tetlet.2003.11.096

upstream raw materials:

trichloromethyl chloroformate

tert-butyl (4R,5R)-4-(4-methoxyphenyl)-2-oxo-1,3-oxazolidine-5-carboxylate

tert-butyl (E)-3-(4-methoxyphenyl)prop-2-enoate

tert-butyl (2R,3R)-3-amino-2-hydroxy-3-(4-methoxyphenyl)propanoate

Downstream raw materials:

(4R,5R)-cytoxazone

methyl (4R,5R)-4-(4-methoxyphenyl)-1,3-oxazolidine-2-one-5-carboxylate